Gambling for Love
by suspensegirl
Summary: Based off early S6 spoilers - "Chuck and I aren't together." Dan knows all too well what happens when Chuck & Blair decide to 'wait'. CB, CBD


A/N: Alright, since the spoilers/major speculations started coming out around when filming started, I've been making notes of a series of one-shots I could write based on them, but the official synopsis for the premiere just bit my head straight off and I can't resist any longer or dally about trying to figure out the exact details of every little bit of what that string of stories might have been.

The basic plot/summary of this story is this: Dan is homeless because Rufus & Ivy are having an affair at the Humphrey loft. CB have promised themselves to each other, but aren't really physically together, because they have to figure out what they want as individual people so they don't end up in a mess like the last time they were together. Also, aside from destroying everyone's lives with his upcoming book (though this point will be less focused on), Dan takes the knowledge of CB not being officially together to his advantage by trying to move in on B again, since he's still hung up on her.

As you can see, this fic is largely based on the spoilers we've gotten recently – also the promos. I need to channel my emotions somewhere. Hope you enjoy.

*I own nothing. No copyright infringement intended

…

**Ch.1—**

"You chose Chuck over me…"

_Dan Humphrey. In her face, accusing her and demanding an explanation._

She knew she deserved it, but after ignoring all the e-mails she'd sent him trying to explain things at the beginning of summer and not face-to-face confronting her until she'd demanded he help with finding Serena, he deserved at least a little shunning on her end. She'd tried to give him closure, but he'd refused it. And now that she was with Chuck – as far as he knew, Dan was trying to make her feel guilty.

"Is that why you've been acting so rude? Because you're mad about Chuck?" she demanded. Because he _had_ been snappy and rude. She'd seen Serena slap him. She'd slapped him herself. He was saying things that made it clear he was bitter and now he'd finally cooled off enough to tell her what was causing the bomb explosion.

She _should_ be relieved, she told herself, because she _did_ still care about him and she _had_ kind of left him high and dry – even if he _had_ given her an ultimatum. She detested those. But she didn't feel relieved. She was just pissed.

"I just want to know why you picked him. Was our relationship doomed from the start? Did you even like me? Or did you just decide to jump on board because I loved you?"

She sighed testily, not letting his word _loved_ get to her. It wasn't that it was in past tense; it was that it had gotten to that stage for him period. She wished it hadn't, because from the start she knew it wouldn't for her.

"_Tell me_," he demanded, and now he was getting snappy again, so she just came out with it.

"Chuck and I _aren't_ together," she said, her voice rising a little.

His brows furrowed and he relaxed slightly. "You're not?" he asked, confused, wondering now if he should've opened one of those many e-mails she'd sent him at the beginning of the summer trying to explain herself and why she hadn't shown up that night – and not deleted them the second he saw who they were from.

She sighed again and rolled her eyes. "No," she said tightly.

"Are you…still…"

Now he was beginning to falter, because what if she was just heartbroken over him never responding and had been yearning for him to just come to her and ask what had happened? Maybe she'd changed her mind at the last second and he'd just been so irritated from his encounter with Serena that he hadn't taken the time to think that maybe at the end of the day Blair had chosen _him_ and had taken his rejection to show he didn't want her anymore.

He'd dug himself deep. And right at that moment he wanted to curse Serena and tell her straight to her face how much he regretted even coming into contact with her period, let alone dating her.

"No, you moron, I'm not still 'in love' with you," she snapped, stepping back when he tried to take a step towards her. "Never was, to be honest," she said, crossing her arms across her chest. "I was 'in like' with you, I guess. We had something. I never lied to you about how I felt in that regard, but whatever I felt for you is gone, so if you think I've been moping around all summer missing you, think again."

_And just like that his little flame of hope flickering in the darkness went out._

So much for his theory.

"If you _must_ know, I _did_ go after Chuck, and we _were_ together temporarily. Now we're waiting," she said matter-of-factly.

"_Waiting_?" he asked dubiously, though that flicker of hope was starting up again. He knew all too well what happened when Chuck and Blair were 'waiting'. No matter how long their relationships with other people lasted, they always happened when they weren't together.

He tried not to let the hope of maybe getting a second shot with Blair show in a smile on his face.

"Yes, _waiting_," she said irritated. "We want to get it right this time. If we can't figure out what we want as individual people, how are we supposed to last as a couple in the long run?" she quoted from Chuck.

Straight from Chuck's mouth. Those were the exact words he'd told her after they'd come down from their high of six straight rounds of sex and sleeping through the night.

He'd taken her out to breakfast – their thing since the sixth grade, and he'd told her flat out that while it had been bitter and harsh, what he'd originally told her on the rooftop of The Empire had been the truth. There would be no solid future for the two of them, if he didn't have his own future figured out – and hers either. Yes, she'd just inherited her mother's company, but it wasn't like baking a cake. You had to learn the ropes, get experience before you just plunged into a life-long commitment with your significant other.

She knew it was right, and that it was smart, because she'd meant it when she'd told Serena that the next person she said 'I love you' to would be the last. And she did not plan on having another divorce on her record, especially since she knew that would be the end result for any other marriage she would attempt because never in the history of the last four years had she _truly_ gotten over Chuck.

But that didn't mean she wasn't devastated, because she was. After all the crap they had gone through, she truly believed that her following Chuck all the way to Monte Carlo meant it would be the last time they would have to keep each other at arm's length and that they could finally be together, that this would be it.

Maybe pre-maturing Chuck would have shared that sentiment, though he certainly hadn't early on in their senior of high school, but not this Chuck. This Chuck was smart and responsible. He thought things through and he wanted them to work.

But it still sucked, because it had been four months since they'd had their little _talk_ and all she could think about was how she'd give the world just to be able to sleep in the same bed with him, to let him hold her. The idea of kissing – or better yet – having him make love to her was overwhelming.

"What makes you think the two of you won't just move on in the process of 'waiting'?" Dan mocked, bringing her back to reality.

Her eyes narrowed. "I'm not getting back with you, Humphrey," she said and started to move past him. He was startled and nearly fell over but still managed to turn his head when she spun around to say one last thing. "And for your information, _this_ is what's keeping us from moving on." She pulled out the chain around her neck that had been seemingly invisible before and on it was a dazzling ring.

He couldn't examine if it looked very much like an engagement ring or not because she tucked it back into her shirt just as quickly as she'd taken it out, but it definitely didn't look like something that could be easily disregarded.

"A _promise_ ring?" he asked, trying to sound unimpressed.

She raised her eyebrows by way of an answer and changed the subject.

"I'm going to go find Serena. We may have stopped her never-should-have-been-contemplated-without-informing-me-first wedding, but if at least _one_ of us doesn't see where she's headed off to, we may have difficulty finding her again."

And with that, she turned away from Dan's somewhat undetermined expression in search of her best friend – who had apparently decided to go all _Inside_ on her.

…

He'd heard what she said. He'd heard every word. Or, at least every word until he hadn't been able to listen anymore. Which had been at the beginning. The very beginning. Which meant he was probably overreacting completely.

"_Chuck and I aren't together."_

He didn't know why that hurt so much. It had been his idea after all, and it was a good one. But the way she said it…it was so…defensive, like she couldn't believe her most recent ex had just accused her of such a ridiculous accusation.

It made his insides burned, because if she planned on having this type of mindset until they figured out themselves individually and were ready to be together, he didn't know if he would be too comfortable being with her. He obviously wouldn't be able to stop himself if she would have him – which he would find out when he got down on bended knee after however long it would take for them to really _find_ _themselves_, but…well, her response to Dan just bothered him.

That was it. Plain and simple.

"Serena's leaving!" Blair announced, coming into the room suddenly. Her eyes looked slightly panicked but the rest of her was completely put together. She was very much in charge of the Serena situation. She was just trying her hardest to invoke the essence of being frazzled to anyone who would listen.

"Nate's going to follow her," Chuck said, turning around slowly. "His limo is right behind her car."

Her brows furrowed and she suddenly came to a stop.

"Didn't we all come in the same limo?" she asked, confused.

He shrugged. "Nate's only going to find her whereabouts and then report back. Besides, it's not like I can't get us another form of transportation if we really need to get out of here as soon as possible. Personally, an open bar is an open bar and should be taken advantage of."

She smiled slightly at his humor but then frowned almost immediately after and walked towards him.

"Is something wrong?" she asked, and he wished she didn't know him so well. Scratch that, one of the best things about the two of them was that they knew and understood each other so well. But right now was not the time for him to be getting insecure about their 'arrangement'.

"I heard you talking with Humphrey," he said bluntly. Because how could he hide this from her? The Chuck from a year ago would've hidden his feelings down deep until they bubbled up to the surface and made him explode. But new Chuck knew to be honest and that it was the best thing.

Honesty and Trust were _key_ things, whether they were currently romantically involved or not.

Her brows furrowed, though she knew full well what he was referring to.

"Out on the deck." He gestured his head in that general direction. "About _us_."

Her eyes widened briefly. "He deserved an explanation, Chuck," she said softly.

He took a deep breath. "Look, I know we decided to wait…"

Her eyes lit up briefly, wondering hopefully if only for a moment that he'd decided to change his mind on the subject.

"…and I still think we should…"

She tried to hold back the disappointment she felt from his conclusion.

"…but I don't know if I feel comfortable with you being so offended by accusations about us being together."

Her lips parted, shocked by the words coming out of his mouth.

"I mean, I know we're not technically _together_ in that sense of the word right now, but you're it for me, Blair, and I'm going to feel that way about you until we get together again, until it's official, and hopefully for a really long time after that, till death do us part I believe is what is said in general wedding vows, and I'm going to mean it. I'm going to be obvious about it too."

"Chuck…" she breathed, just trying to catch her breath. He was so fierce how he talked to her now, so boldly romantic that it felt like he was trying to win her over again and it made her swoon, because he didn't need to and he never would again.

He paused for a moment, seeming to need to catch his own breath too, but for obvious different reasons.

"So, it kind of bothers me that you don't have that same kind of sense of where we stand." He shoved his hands into his pockets, and then after awhile of silence looked back up at her. "I won't be the guy you're ashamed of having in your past when we're not together. I _won't_."

"Hey-" She covered four fingers over his lips to stop him from talking. He was only hurting both them by voicing his continued assumptions. "That's not how I feel at all," she whispered, because now she was very, very close to him. When his eyes shifted to hers, she dropped her hand back to her side and took one tiny step back.

"So then why did you say it like that?" he asked quietly. She saw the danger in his eyes though, the hurt. She knew if he repeated the question his voice would break.

"I don't know what you all heard," she said, looking at his crestfallen face so sadly, "but I also told him that we were waiting and that it wouldn't be like before because you gave me _this_," she said, pulling out the necklace with the ring that shined at him.

"_Blair_," he whispered harshly, eyes telling her to hastily put the necklace away like she'd done some heinous crime by bringing it out.

Her eyebrows furrowed. Now _she_ was hurt.

"You let him see it?" he ground out.

"I flashed it in his face, yes, but I don't think he got a good look." She frowned. "Why? Wasn't it you who just said you were basically going to broadcast it to anyone in a five mile radius that you and I are unofficially official?"

He nodded. "Yes…but…"

"Chuck," she said, taking a step closer and rubbing one hand up and down his arm. "I was defending us _together_, not defending my lack of involvement with you."

He tilted his head to the side, considering her statement.

"If you would've eaves dropped just a little longer, you would've realized that."

He nodded. "You're right. I'm sorry. I…jumped to conclusions."

She smiled softly. "Hey-"

He looked up at her, saw her soothing, warm, _loving_, _committed_ gaze.

"I'm all in," she said gently.

The words alone sent butterflies fluttering in his stomach and chills up his spine. He could've sworn, even under his pastel suit that he had goosebumps, and he knew then that everything had fallen into place and he didn't need to worry anymore. She was on the same page with him. They were on the same wavelength. He wouldn't make the mistake of doubting it again.

"And my bet's on us," he said warmly.

Her eyes were hazy with love as her hand drifted down his arm, nearly touching his hand when a booming voice interrupted their locked gaze.

"Hey, guys," Nate said, walking into the room.

Instantly, she pulled away and they both turned to look at the intruder.

"I know you said I should just come back later, but she's just leaving now…so, do you want to go?" He stopped his direct eye contact to look between the two brunettes and once again realized belatedly that he might have interrupted a private moment. "Oh…am I interrupting something?" he asked, clearly holding back a guilty apology.

Chuck and Blair shared a look but then Blair moved past Chuck and their announcer.

"We'll come now, Archibald," she announced even as she went past him.

Nate looked towards Chuck a little confused, but the brown haired boy just nodded once and moved after his not-really-but-soon-to-be-implied-girlfriend/fiancé/wife.

"_Did_ I interrupt something?" Nate asked warily, finally walking along with his best friend.

"Nothing that needs mentioning," he said, then scanned the crowd once they got outside. "Where's Serena?"

….

She'd just finished getting ready for bed: teeth brushed, hair brushed 100 times, and the perfect pink satin ensemble to sleep in, eye mask ready at hand – when she heard the ding of the elevator doors opening downstairs. Her eyebrows furrowed in confusion but she knew Dorota was fumbling with things farther down the hall, and so decided to attend to the visitor herself.

"I've got it, Dorota," she announced, stepping outside her room to head for the stairs.

And there, in the middle of her foyer was Dan Humphrey, a suitcase at his feet and a cell phone in his hand. She crossed her arms when she reached the bottom of the steps.

"Were you going to _call_ me?" she asked, giving him a once-over of disapproval.

"Sometimes Dorota doesn't take well to certain guests," he explained.

"Sometimes she has good reason."

He sighed. "Look, I just wanted to apologize for the way I acted today. I'm sure it's clear that I'm bitter about the way things ended between us, but I shouldn't have taken it out on you since I'm the one who gave you the option to end it or not in the first place."

"I'm still waiting for the apology," she stated, lips pursed tightly together.

He sighed. "I'm sorry."

"And?" she held out her hand by way of gesture.

His brows furrowed. "And what?"

She laughed lightly. "I'm pretty sure most apologies don't come with a suitcase."

He hung his head briefly and cracked a grin. "You see, the thing is…"

She took a step back, well aware of where his thought process was going.

"No. I _just_ forgave you – or, you just apologized rather. You're not slumming it here, in my house, for _whatever_ reason."

"But…didn't Serena not come back with you?" he asked.

She avoided eye contact. "We still have some differences that need to be resolved, so what!" Her eyes suddenly blazed.

"Well, if she's not staying in her room, then—"

Her eyes widened and yet somehow still glared, so he decided to retract his last sentence, or at least prevent himself from finishing it.

"Don't you have like…a _ton_ of rooms?"

She sighed, contemplating it.

"I don't know why I'm even bothering to ask this question, but why do you need a place to stay to begin with?"

He hesitated. "Things have gotten…_complicated_ at home."

She analyzed his features but realized she couldn't figure anything else out unless she interrogated him for a good 30 seconds – thirty _precious_ seconds she did not intend on wasting.

"_Complicated_," she repeated.

"Yes."

She sighed. "I still don't see why…"

"Blair, please, we were friends once, weren't we?" he reminded her, his eyes pleading.

She tried to look away from the desperation on his face but found herself unable to.

"Yes…"

"If any of your other friends were in this situation, wouldn't you _gladly_ take them in? No matter what _differences_ might need to be reconciled between the two of you?"

She searched her mind for a way out of this, but found she could not, because he was 100% right.

She sighed dramatically. "_Fine_," she said, turning around to head back up the stairs and cursing herself inwardly because if her senses were right - and they usually were, her new houseguest was definitely staring at her ass. "But you're not sleeping in Serena's bedroom," she tossed over her shoulder. "She may not be here now, but she will be eventually and it will not help things if she comes back to see her room has been…Dan-ified."

He nodded. "Noted."

"And _stop_ staring at my ass," she told him once she'd reached the top of the steps. His jaw dropped, but she called out to her maid before he could respond. "Dorota!" she called out. The maid popped up, surprised to see Dan coming up the stairs behind her mistress.

"Yes, Miss Blair?" she asked questioningly.

"Fix Dan a room," she said, waving her arm about in a gesture towards another room. "He'll be staying with us for a little while."

Dorota would've asked her mistress more questions, but Blair had already gone into her room and closed it securely.

Blair popped her head out a moment later. "And _not_ Serena's room," she clarified.

Dorota held her tongue for more questions. "Yes, Miss Blair."

The door to Blair's room shut – almost on a slam – again. Dorota turned to look at Dan. She gave him a once-over and was clearly displeased.

"Why you here?" she demanded.

"It's…complicated."

Dorota's eyes narrowed. For all the months she'd given him a happy smile due to his friendship and then romance with her mistress she knew a schemer when she saw one, and this did not look innocent in the least.

"I won't cause any trouble, Dorota. I promise." He bowed a little, acting like a gentleman, a comically-induced one, which did not put Dorota at ease in the slightest, but she forced herself to remember the fondness she'd held for him only months earlier and give him the benefit of the doubt.

"Right this way, Mr. Dan," she said, turning her back to lead him down the hall.

He paused, looking at the light beneath Blair's bedroom door and then at the crevice along the doorway, thinking things that he should not be thinking, fantasizing about what pre-boyfriend Dan would've deemed innocent and inappropriate all at once.

He was shaken from his thoughts when Dorota called out to him again. He scurried after her, knowing full well that Blair would come bursting out if she became aware that he was not cooperating.

….

A/N: Please review. This will definitely be going on for awhile.


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